Jack Ingram began his music career singing at a privately owned bar near the TCU campus of Fort Worth, Texas which was owned by his friend John Clay Wolfe. Later, during the early 1990s, Jack toured the state of Texas opening for Mark Chesnutt and other acts.[1] His first release was his self-titled album in 1995 via the Rhythmic label, followed by 1995's Lonesome Question. Warner Bros. Records eventually signed him and released a live album entitled Live at Adair's, and re-issued his first two indie albums.[1]

Electric, his second album for Lucky Dog, was also his first album to enter Top Country Albums, despite not producing a chart single. This album was supplemented a year later by an EP entitled Electric: Extra Volts before he left Lucky Dog. Two more live albums followed before he signed to Columbia Records for the release of Young Man in 2004, which accounted for no singles. Another live album, Acoustic Motel, was issued in 2005.

In 2005, Ingram signed to the independent record label Big Machine Records. Under the Big Machine banner, Ingram released a predominantly live album entitled Live: Wherever You Are. His first single release on that record label, "Wherever You Are", became Ingram's first top 40, and later his first Number One single on the U.S. BillboardHot Country Songs charts, as well as the first Number One for the Big Machine label. "Love You", the only other studio track on Live: Wherever You Are, was also released as a single, peaking at No. 12 on the charts. This song was also recorded by Trent Summar & The New Row Mob (whose frontman, Trent Summar, co-wrote it) on their 2005 album Horseshoes & Hand Grenades. This is also where he met famous country music artist Taylor Swift. Jack stated they were developing a relationship though she wasn't interested.

In late 2006, Ingram released a cover of Hinder's song "Lips of an Angel". Ingram's cover peaked at No. 16 on the country charts "Lips of an Angel" was the lead-off single to This Is It, his second album for Big Machine. This album also produced the No. 18 "Measure of a Man" (a Radney Foster co-write) and the No. 24 "Maybe She'll Get Lonely".

In 2008, Ingram appeared at the Argyle Education Foundation Black Diamond Affiar.

According to CMT, Ingram's Big Dreams & High Hopes album has "more guts" and Ellis Paul's "The World Ain't Slowing Down" may be the song that takes Ingram to the "next level".[3] Ingram says "It'll be fun for me to expose people to a fantastic song from an artist who's had a 20-year career of being a very successful folk artist."[4] The song was cut from the album. Its lead-off single "That's a Man" charted in the Top 20, followed by "Barefoot and Crazy," which became his second Top 10 hit. The album's next three singles all failed to enter the Top 40: "Seeing Stars" (a duet with Patty Griffin), "Free" and a re-recording of "Barbie Doll" with guest vocals from Dierks Bentley.

On August 26, 2009, Ingram set a Guinness record for the most radio interviews in one day, when he was interviewed 215 times.[5]

In 2013, Jack teamed up with actor Matthew McConaughey and University of Texas at Austin football coach Mack Brown to create a fundraiser for their favorite children's charities. Dubbed Mack, Jack & McConaughey, the affair was held April 11–12 at Austin's ACL Live at the Moody Theater and featured a gala, golf tournament, fashion show and two nights of music.[8] Mack, Jack & McConaughey returned in 2014.[9]

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